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Greenwood Holiday Rentals

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Our top choices for Greenwood holiday rentals

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (63 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is AU$125
includes taxes & fees
25 June - 26 June
Affordable Suites of America Waynesboro

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (245 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is AU$155
includes taxes & fees
8 July - 9 July
Valley Extended Suites

The Reserve at 151

The Reserve at 151
2.0 star property
Afton
The price is AU$759
includes taxes & fees
24 June - 25 June
The Reserve at 151

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (18 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is AU$293
includes taxes & fees
24 June - 25 June
Love Ridge Mountain Lodging

SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
10.0 out of 10, Exceptional, (1 review)
"Our stay was perfect. Hotels.com really messed up the booking and I almost didn’t have a place to stay. The host at this property held the room for me and we handled everything directly. He was great, the room was spectacular!"
United States
Crystal
The price is AU$186
includes taxes & fees
29 June - 30 June
SONSAK - MONTICELLO

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Wintergreen Resort
10.0 out of 10, Exceptional, (116 reviews)
"Great location"
United States
Chrissy R.
The price is AU$476
includes taxes & fees
7 July - 8 July
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (70 reviews)
"The apartment was beautifully decorated and immaculately clean. It was close to everything we intended to get to and we appreciated how easy it was to check in and check out. It was so comfortable and homey. "
United States
Natalie
The price is AU$349
includes taxes & fees
24 June - 25 June
Stay in Crozet Train Suite in Downtown Crozet

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (155 reviews)
"Lisa we are happy for staying at your places it awesome and we had great time, thank you let us use your home"
United States
Issac S.
The price is AU$359
includes taxes & fees
8 July - 9 July
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Roseland
10.0 out of 10, Exceptional, (106 reviews)
"This place is such a gem. Stunning property, clean, and comfortable. You can tell the hosts take a lot of pride in this place. Loved it. "
United States
Warren
The price is AU$283
includes taxes & fees
24 June - 25 June
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (110 reviews)
"The house was very centrally located in Crozet, an easy walk to restaurants and the brewery. It was very cosy and had lots of little extras like coffee and dog treats! We were there for one night for the walk through for our daughters wedding at one of the local vineyards and it was perfect for our needs. "
United States
Helen S.
The price is AU$476
includes taxes & fees
24 June - 25 June
High Street | Walk to Everything Crozet | Pet-Friendly

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (45 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
The price is AU$415
includes taxes & fees
24 June - 25 June
Panoramic Peak: Wintergreen Condo with Views

Total Privacy - H’Owl at the Moon Farm & Cabin

Total Privacy - H’Owl at the Moon Farm & Cabin
Schuyler
10.0 out of 10, Exceptional, (184 reviews)
"The cabin was amazing. It was so peaceful and quiet. The cabin was in a prefect place to view wildlife and trails to view the additional property. The amenities were great and everything worked as expected. The owner was responsive and very nice. Would stay here again. "
United States
Nova G.
The price is AU$588
includes taxes & fees
24 June - 25 June
Total Privacy - H’Owl at the Moon Farm & Cabin

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (54 reviews)
"Very good host, good with communication! Nice clean place to stay and close to a lot of the places we were wanting to go!"
United States
Meredith T.
The price is AU$304
includes taxes & fees
30 June - 1 July
Where the Trail Ends

Ivy Rose Cottage nestled b/t Cville & Vineyards

Ivy Rose Cottage nestled b/t Cville & Vineyards
Charlottesville
10.0 out of 10, Exceptional, (80 reviews)
"The cabin was very clean. Very cozy. We definitely enjoyed our time there and would love to come back."
United States
jeramy p.
The price is AU$479
includes taxes & fees
24 June - 25 June
Ivy Rose Cottage nestled b/t Cville & Vineyards

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (108 reviews)
"Nice place!"
United States
Gregory G.
Endless Mountain Top Views from All The Way Up!

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (30 reviews)
"Well supplied with essentials , charming"
United States
Beth
The price is AU$454
includes taxes & fees
24 June - 25 June
The Cottage @ Afton Mountain- Close to Wineries!

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (35 reviews)
"Condo was as advertised, perfect for a quick trip up to Wintergreen!"
United States
Jason L.
The price is AU$388
includes taxes & fees
24 June - 25 June
Wintergreen Condo -Steps to Ski and restaurants

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (324 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is AU$374
includes taxes & fees
16 July - 17 July
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (128 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
The price is AU$364
includes taxes & fees
24 June - 25 June
Escape to the Blue Ridge Mountains at Wine-tergreen!

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (66 reviews)
"Such a great little place! Quick drive to town, but far enough for a quiet night. Room had everything we needed (and then some) for a short stay, and all the animals were the sweetest added bonus. Would absolutely stay here again if we’re ever back in the area."
United States
Rebekah
The price is AU$166
includes taxes & fees
29 June - 30 June
The Firefly Springhouse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Greenwood Hotel Reviews

Find out more about Greenwood

Everything you need to know about Greenwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Greenwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood holiday rentals we have selected for you start as low as AU$125 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its wineries.

What are some of the best holiday rentals that Greenwood has to offer?

Beautiful New Townhome with Mountain Views. Close to downtown!: This holiday home rental outside of Greenwood offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Greenwood?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Greenwood stay.

What’s there to see and do in Greenwood?

Explore the area and family-friendly sights such as War Fields, or get out into nature at a spot like Rockfish Gap Entrance Shenandoah. In the wider area, you’ll find Pollak Vineyards and King Family Vineyards.

What’s a holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips.